US7326369B2 - Low stress conductive adhesive - Google Patents

Low stress conductive adhesive Download PDF

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Publication number
US7326369B2
US7326369B2 US11/073,778 US7377805A US7326369B2 US 7326369 B2 US7326369 B2 US 7326369B2 US 7377805 A US7377805 A US 7377805A US 7326369 B2 US7326369 B2 US 7326369B2
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United States
Prior art keywords
composition
epoxy
weight percent
conductive
functional acrylic
Prior art date
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US11/073,778
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US20060197066A1 (en
Inventor
Chih-Min Cheng
Andrew Collins
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
National Starch and Chemical Investment Holding Corp
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Priority to US11/073,778 priority Critical patent/US7326369B2/en
Assigned to NATIONAL STARCH AND CHEMICAL INVESTMENT HOLDING CORPORATION reassignment NATIONAL STARCH AND CHEMICAL INVESTMENT HOLDING CORPORATION ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHENG, CHIH-MIN, COLLINS, ANDREW
Priority to JP2006057140A priority patent/JP4875386B2/ja
Priority to CN2006100583710A priority patent/CN1831073B/zh
Priority to AT06004488T priority patent/ATE465497T1/de
Priority to KR1020060020908A priority patent/KR101325083B1/ko
Priority to EP06004488A priority patent/EP1701361B1/fr
Priority to TW095107344A priority patent/TWI382076B/zh
Priority to DE602006013734T priority patent/DE602006013734D1/de
Publication of US20060197066A1 publication Critical patent/US20060197066A1/en
Publication of US7326369B2 publication Critical patent/US7326369B2/en
Application granted granted Critical
Assigned to HENKEL KGAA reassignment HENKEL KGAA ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: INDOPCO, INC., NATIONAL STARCH AND CHEMICAL INVESTMENT HOLDING CORPORATION
Assigned to HENKEL AG & CO. KGAA reassignment HENKEL AG & CO. KGAA CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: HENKEL KGAA
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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01C—PLANTING; SOWING; FERTILISING
    • A01C1/00—Apparatus, or methods of use thereof, for testing or treating seed, roots, or the like, prior to sowing or planting
    • A01C1/02—Germinating apparatus; Determining germination capacity of seeds or the like
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/20—Conductive material dispersed in non-conductive organic material
    • H01B1/22—Conductive material dispersed in non-conductive organic material the conductive material comprising metals or alloys
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
    • A01G31/00—Soilless cultivation, e.g. hydroponics
    • A01G31/02—Special apparatus therefor
    • A01G31/06—Hydroponic culture on racks or in stacked containers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J9/00—Adhesives characterised by their physical nature or the effects produced, e.g. glue sticks
    • C09J9/02—Electrically-conducting adhesives
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
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    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/30—Assembling printed circuits with electric components, e.g. with resistor
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    • H05K3/321—Assembling printed circuits with electric components, e.g. with resistor electrically connecting electric components or wires to printed circuits by conductive adhesives
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    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
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Definitions

  • This invention relates to compositions that are suitable for use as conductive materials in microelectronic devices or semiconductor packages to provide electrically stable interconnections.
  • Conductive compositions are used for a variety of purposes in the fabrication and assembly of semiconductor packages and microelectronic devices.
  • conductive adhesives are used to bond integrated circuit chips to substrates (die attach adhesives) or circuit assemblies to printed wire boards (surface mount conductive adhesives).
  • solder alloy which is so called eutectic solder containing by weight 63% tin and 37% lead. It is applied to the circuit board as a paste or a solder preform which is heated to above its melting temperature (183° C.) to let solder paste melt and form joint. Alternatively, the board is passed over a molten wave of solder to form joints to bond the electrical components to the circuit board. In either case, a flux material is used to remove surface oxidation from metallic surfaces and allow the molten solder to strongly bond to the surfaces and form reliable solder joints with excellent impact resistance. While the solder technology has existed for many decades, it has several shortcomings. Lead in the alloy is not environmental friendly.
  • Conductive adhesives offer several advantages over traditional solder assembly due to the absence of lead, low processing temperatures and a simplified assembly process that does not require solder flux and subsequent flux cleaning steps.
  • desired properties of conductive adhesives are long work life at room temperature, relatively low curing temperature and relatively short curing time, good rheology for screen printing, sufficient conductivity to carry an electric current when cured, acceptable adhesion to the substrate when cured, stable electrical resistance at high temperature and humidity over long periods of time, and good impact strength.
  • Conductive adhesives are particularly useful for large area assemblies intended for various microwave applications which require bonding of a FR4 or ceramic circuit board to a metal substrate having an aluminum or copper core. In such applications, conductive adhesives provide electrical integrity, bond-line consistency and improved thermal dissipation that insures compliance with regulatory requirements, minimizes losses, minimizes distortion of high frequency digital signals and maintains low impedance to the ground plane.
  • Film adhesives are utilized as low temperature process alternatives to solder and create a consistent ground path between an electrical circuit board and a metal backer. Film conductive adhesives are preferred for large area assembly due to their consistency in bond line thickness, low flow properties and availability as an intricate die cut part. Film adhesives are received by the end assembler in a B-stage condition having been pre-cut to the dimensions of the desired PCB.
  • the carrier substrate usually MYLAR, is removed from the film, the film is placed between the substrates to be bonded, and the package is bonded together under elevated temperature and pressure. Further, because film adhesives have a much higher viscosity than paste adhesives, settling of the filler is not a concern when the film is stored at room temperature for an extended period of time.
  • Film adhesive having high strength are generally high modulus adhesives with limited flexibility. Such films having a high modulus and high cross-link density create a high stress condition due to extreme differences in the coefficient of thermal expansion between the board and the metal heat sink after cure. The result of the high stress is a high degree of warpage in the final assembly. Film adhesives that offer low stress are typically lower in modulus and also lower in adhesion strength. Consequently, commercially available flexible films are lower in adhesion strength than non-flexible films.
  • Paste conductive adhesives may also be used to bond together large areas, especially if the adhesive is screen printed onto the substrate. The screen printing enables high volume manufactures and limits waste. Paste conductive adhesives may also be B-stageable so that they may be pre-applied on the component in a manner similar to a film, stored, and then heated for final bonding. The rheology of paste adhesives must be monitored to insure accurate deposits of adhesive on the circuit boards. Likewise, the rheology of the paste must be monitored to avoid bleed out or slumping during the B-stage or cure processes.
  • the adhesive would have a combination of superior adhesion to common flexible film adhesives and superior stress reduction as compared to common high strength film adhesives.
  • This invention is a low stress isotropic conductive film or paste adhesive that comprises a) one or more functional acrylic copolymers; b) epoxy; and c) conductive filler. Additional ingredients, such as adhesion promoters, curing agents and conductivity enhancers may also be utilized.
  • the conductive film adhesive of the invention provides higher adhesion strength than traditional flexible conductive film adhesives and a lower stress between the bonded components than existing high adhesion strength conductive films.
  • the conductive adhesive of the present invention comprises a) one or more functional acrylic copolymers or terpolymers; b) epoxy; and c) conductive filler.
  • one or more adhesion promoters, curing agents and conductivity additives are also included.
  • functional acrylic copolymers are referred to, it is to be understood that the functional acrylic may also comprise a terpolymer.
  • the functional acrylic copolymer of the invention is soluble in coating solvent and thus enables a low stress, high strength film forming or paste adhesive.
  • the preferred acrylic copolymer is a saturated polymer and thus more resistant to oxidation, aging and deterioration than typical rubber reinforcing resins such as carboxyl-terminated butadiene nitrile rubber.
  • the composition of the copolymer is preferably butyl acrylate-ethyl acrylonitrile or butyl acrylate-co-ethyl acrylonitrile or ethyl acrylate-acrylonitrile to provide high molecular weight polymerization.
  • the copolymer preferably has hydroxyl, carboxylic acid, isocyanate or epoxy functionality to improve the solvent and epoxy compatibility.
  • the molecular weight of the copolymer is high and preferably in the range of about 200,000 to about 900,000.
  • the glass transition temperatures (Tg) of the copolymer are low relative to room temperature and preferably within the range of about 30° C. to about ⁇ 40° C. While various functional acrylic copolymers may be utilized, a preferred functional acrylic copolymer is TEISAN RESIN SG80H, commercially available from Nagase ChemteX Corporation of Osaka, Japan.
  • the preferred epoxy resin for use with the present invention include monofunctional and multifunctional glycidyl ethers of Bisphenol-A and Bisphenol-F, aliphatic and aromatic epoxies, saturated and unsaturated epoxies, or cycloaliphatic epoxy resins or a combination thereof.
  • a most preferred epoxy resin is bisphenol A type resin. These resins are generally prepared by the reaction of one mole of bisphenol A resin and two moles of epichlorohydrin.
  • a further preferred type of epoxy resin is epoxy novolac resin. Epoxy novolac resin is commonly prepared by the reaction of phenolic resin and epichlorohydrin.
  • Dicyclopentadiene-phenol epoxy resin, naphthalene resins, epoxy functional butadiene acrylonitrile copolymers, epoxy functional polydimethyl siloxane, epoxy functional copolymers and mixtures thereof are additional types of epoxy resins which may be employed.
  • Commercially available bisphenol-F type resin is available from CVC Specialty Chemicals, Maple Shade, N.J., under the designation 8230E and Resolution Performance Products Ltd. under the designation RSL1739.
  • Bisphenol-A type epoxy resin is commercially available from Resolution Performance Products Ltd. as EPON 828, and a blend of bisphenol-A and bisphenol-F is available from Nippon Chemical Company under the designation ZX-1059.
  • the electrically conductive material may comprise conductive fillers.
  • Exemplary conductive fillers are silver, copper, gold, palladium, platinum, carbon black, carbon fiber, graphite, aluminum, indium tin oxide, silver coated copper, silver coated aluminum, bismuth, tin, bismuth-tin alloy, metallic coated glass spheres, silver coated fiber, silver coated spheres, antimony doped tin oxide, carbon nanotubes, conductive nanofiller, conductive oxides and mixtures thereof.
  • suitable flow additives include silicon polymers, ethyl acrylate/2-ethylhexyl acrylate copolymers, alkylol ammonium salt of acid phosphoric acid esters of ketoxime or mixtures thereof.
  • Suitable adhesion promoters include various forms of silane.
  • Suitable rheology modifiers include thermoplastic resin and preferably polyvinyl acetal.
  • Suitable conductivity additives include anhydride, glutaric acid, citric acid, phosphoric acid and other acid catalysts.
  • Suitable curing agents include, but are not limited to, Lewis Acids, anhydrides, amines, imidazoles, dicyandiamide and mixtures thereof.
  • the isotropic conductive adhesive composition of this embodiment of the invention contains up to about 4 to 19 weight percent of a functional acrylic copolymer; about 60 to 95 weight percent of a conductive filler; about 1 to 10 weight percent of an epoxy; about 0 to 10 weight percent of a curing agent; about 0 to 5 weight percent of conductivity additive; and about 0 to 5 weight percent of adhesion promoters, flow additives, rheology modifiers or other additives for a total of 100 weight percent.
  • the functional acrylic copolymer is present in the range of about 12 to 18 weight percent
  • the conductive filler is present in the range of about 70 to 90 weight percent
  • the epoxy is present in the range of about 2 to 8 weight percent
  • the curing agent is present in the range of about 0.1 to 3 weight percent
  • the conductivity additive is present in the range of about 0.01 to 1 weight percent and the other additives are present in the range of about 0 to about 5 weight percent.
  • Example 1 A functional acrylic copolymer according to the present invention was formulated with the ingredients in Table 1.
US11/073,778 2005-03-07 2005-03-07 Low stress conductive adhesive Active 2025-06-22 US7326369B2 (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
US11/073,778 US7326369B2 (en) 2005-03-07 2005-03-07 Low stress conductive adhesive
JP2006057140A JP4875386B2 (ja) 2005-03-07 2006-03-03 低応力導電性接着材
CN2006100583710A CN1831073B (zh) 2005-03-07 2006-03-03 低应力导电胶粘剂
TW095107344A TWI382076B (zh) 2005-03-07 2006-03-06 低應力導電性黏著劑
KR1020060020908A KR101325083B1 (ko) 2005-03-07 2006-03-06 저응력 도전성 접착제
EP06004488A EP1701361B1 (fr) 2005-03-07 2006-03-06 Adhesif conducteur à faible contrainte
AT06004488T ATE465497T1 (de) 2005-03-07 2006-03-06 Spannungsarmer leitfaehiger klebstoff
DE602006013734T DE602006013734D1 (de) 2005-03-07 2006-03-06 Spannungsarmer leitfaehiger Klebstoff

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US11/073,778 US7326369B2 (en) 2005-03-07 2005-03-07 Low stress conductive adhesive

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US20060197066A1 US20060197066A1 (en) 2006-09-07
US7326369B2 true US7326369B2 (en) 2008-02-05

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US (1) US7326369B2 (fr)
EP (1) EP1701361B1 (fr)
JP (1) JP4875386B2 (fr)
KR (1) KR101325083B1 (fr)
CN (1) CN1831073B (fr)
AT (1) ATE465497T1 (fr)
DE (1) DE602006013734D1 (fr)
TW (1) TWI382076B (fr)

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US20100044088A1 (en) * 2006-07-05 2010-02-25 Ablestik (Japan) Co. Ltd. Conductive adhesive
US20120114934A1 (en) * 2009-05-13 2012-05-10 Megumi Kodama Bonding sheet
US8895865B2 (en) 2012-09-07 2014-11-25 Conor P. Lenahan Conductive connections allowing XYZ translation
US9011732B2 (en) 2010-05-26 2015-04-21 Paul McGrath Conductive adhesive
US20160194525A1 (en) * 2013-08-06 2016-07-07 Senju Metal Industry Co., Ltd. Electrically Conductive Adhesive Agent, Joined Body, and Joint
US9449938B2 (en) 2013-09-30 2016-09-20 Henkel IP & Holding GmbH Conductive die attach film for large die semiconductor packages and compositions useful for the preparation thereof
WO2022043160A1 (fr) 2020-08-27 2022-03-03 Henkel Ag & Co. Kgaa Formulation époxy à un composant (1k) électroconductrice

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CN101275060B (zh) * 2007-03-30 2012-06-20 清华大学 导电胶带及其制造方法
CN101323759B (zh) * 2007-06-15 2014-10-08 清华大学 导电胶带及其制造方法
US8609471B2 (en) * 2008-02-29 2013-12-17 Freescale Semiconductor, Inc. Packaging an integrated circuit die using compression molding
JP5390881B2 (ja) * 2008-03-04 2014-01-15 リンテック株式会社 粘着剤組成物及び粘着シート
JP5339284B2 (ja) 2008-03-04 2013-11-13 リンテック株式会社 粘着剤組成物及び粘着シート
KR101410447B1 (ko) * 2008-03-06 2014-06-20 김종현 전도성이 우수한 전자부품 실장용 전도성 페이스트 및 그제조방법
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KR20060097610A (ko) 2006-09-14
TW200704743A (en) 2007-02-01
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JP2006249426A (ja) 2006-09-21
ATE465497T1 (de) 2010-05-15
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TWI382076B (zh) 2013-01-11
CN1831073B (zh) 2012-01-18
CN1831073A (zh) 2006-09-13

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